5α-cholestadien-(8.24)-one-(3) | 27192-37-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5α-cholestadien-(8.24)-one-(3)
• 英文别名: 5α-Cholestadien-(8.24)-on-(3)；5alpha-Cholesta-8,24-dien-3-one；(5S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,4,5,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 27192-37-6
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: AUNLIRXIJAVBNM-ZSBATXSLSA-N

物化性质

• 沸点：
  480.3±44.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5α-cholestadien-(8.24)-one-(3) 在 盐酸 、 氯仿 、 乙酸乙酯 、 异丙醇 、 甲苯 、 铂 作用下， 生成 5α（H）-Cholestan-3α醇
  参考文献：
  名称：

  Wieland; Benend, Chemische Berichte, 1942, vol. 75, p. 1708,1714

  摘要：

  DOI：
• 作为产物：
  描述：

  (3S,5S,10S,13R,14R,17R)-10,13-二甲基-17-[(2R)-6-甲基庚-5-烯-2-基]-2,3,4,5,6,7,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-醇 在 环己酮 、 aluminum isopropoxide 、 甲苯 作用下， 生成 5α-cholestadien-(8.24)-one-(3)
  参考文献：
  名称：

  Wieland; Rath; Benend, Justus Liebigs Annalen der Chemie, 1941, vol. 548, p. 19,29

  摘要：

  DOI：

文献信息

• A comprehensive machine-readable view of the mammalian cholesterol biosynthesis pathway
  作者：Alexander Mazein、Steven Watterson、Wei-Yuan Hsieh、William J. Griffiths、Peter Ghazal

  DOI：10.1016/j.bcp.2013.03.021

  日期：2013.7

  that describes the cholesterol biosynthesis pathway (the mevalonate, the Kandutch-Russell and the Bloch pathway) and shunt pathway that leads to 24(S),25-epoxycholesterol synthesis. The diagram has been produced using the Systems Biology Graphical Notation (SBGN) and is available in the SBGN-ML format, a human readable and machine semantically parsable open community file format.

  胆固醇生物合成是健康和疾病中众多生物过程的中心代谢中心。现有文献中缺乏对胆固醇通路如何构建以及它如何与其他通路系统相互作用的详细、综合的单一视图描述。在这里，我们对现有文献进行了系统回顾，并提供了详细的途径图，描述了胆固醇生物合成途径（甲羟戊酸、Kandutch-Russell 和 Bloch 途径）和导致 24(S),25-环氧胆固醇合成的分流途径. 该图是使用系统生物学图形符号 (SBGN) 生成的，并以 SBGN-ML 格式提供，这是一种人类可读且机器语义可解析的开放社区文件格式。
• Closing the Gap: Identification of Human 3-Ketosteroid Reductase, the Last Unknown Enzyme of Mammalian Cholesterol Biosynthesis
  作者：Zrinka Marijanovic、Daniela Laubner、Gabriele Möller、Christian Gege、Bettina Husen、Jerzy Adamski、Rainer Breitling

  DOI：10.1210/me.2002-0436

  日期：2003.9

  cholesterol-deficiency disorders. We conclude that HSD17B7 participates in postsqualene cholesterol biosynthesis, thus completing the molecular cloning of all genes of this central metabolic pathway. In its function as the 3-ketosteroid reductase of cholesterol biosynthesis, HSD17B7 is a novel candidate for inborn errors of cholesterol metabolism.

  由HSD17B7基因编码的蛋白质最初被描述为催乳激素受体相关的蛋白质和17β-羟类固醇脱氢酶（HSD）7型。先前已报道了其在体外合成17β-雌二醇的能力。然而，我们证明了HSD17B7是酵母3-酮类固醇还原酶Erg27p的直系同源物，并在体外使用还原的烟酰胺腺嘌呤二核苷酸磷酸作为辅因子将zymosterone转换为zymosterol。人和鼠类HSD17B7在缺乏Erg27p的酵母菌株中的表达可补充细胞的3-酮类固醇还原酶缺乏症，并在缺乏甾醇的培养基上恢复生长。HSD17B7与绿色荧光蛋白的融合体位于内质网，即角鲨烯胆甾醇生成后的位置。HSD17B7在胆固醇代谢中的作用的进一步关键证据是，其观察到的鼠直向同源物与羟甲基-戊二酰辅酶A还原酶，固醇生物发生的限速酶和在先天性胆固醇缺乏症的发病机理中涉及的组织中特异性表达“α-淀粉样蛋白”。我们得出的结论是，HSD17B7参与角鲨烯后胆固醇的生物
• The gene mutated in bare patches and striated mice encodes a novel 3β-hydroxysteroid dehydrogenase
  作者：Xiao Yu Liu、Andrew W. Dangel、Richard I. Kelley、Wei Zhao、Paul Denny、Marc Botcherby、Bruce Cattanach、Jo Peters、Patricia R. Hunsicker、Ann-Marie Mallon、Mark A. Strivens、Rachael Bate、Webb Miller、Michael Rhodes、Stephen D.M. Brown、Gail E. Herman

  DOI：10.1038/9700

  日期：1999.6

  X-linked dominant disorders that are exclusively lethal prenatally in hemizygous males have been described in human and mouse1. None of the genes responsible has been isolated in either species. The bare patches (Bpa ) and striated (Str) mouse mutations were originally identified in female offspring of X-irradiated males2,3. Subsequently, additional independent alleles were described. We have previously mapped these X-linked dominant, male-lethal mutations to an overlapping region of 600 kb that is homologous to human Xq28 (ref. 4) and identified several candidate genes in this interval5. Here we report mutations in one of these genes, Nsdhl, encoding an NAD(P)H steroid dehydrogenase-like protein, in two independent Bpa and three independent Str alleles. Quantitative analysis of sterols from tissues of affected Bpa mice support a role for Nsdhl in cholesterol biosynthesis. Our results demonstrate that Bpa and Str are allelic mutations and identify the first mammalian locus associated with an X-linked dominant, male-lethal phenotype. They also expand the spectrum of phenotypes associated with abnormalities of cholesterol metabolism.

  人类和小鼠中都有X连锁显性遗传病，这种病在单倍体雄性中仅在产前致死，1。但在这两种物种中，都没有分离出相关的基因。裸斑（Bpa）和条纹（Str）小鼠突变最初是在X射线照射雄性小鼠的雌性后代中发现的2,3。随后，又发现了其他独立等位基因。我们之前将这些X连锁显性、雄性致死突变定位到与人类Xq28同源的600kb重叠区域（参考文献4），并在此区间内确定了几个候选基因5。在此，我们报告了其中一种基因Nsdhl的突变，该基因编码一种NAD（P）H类固醇脱氢酶样蛋白，在两个独立的Bpa和三个独立的Str等位基因中都有突变。对患病Bpa小鼠组织中的固醇进行定量分析，证实了Nsdhl在胆固醇生物合成中的作用。我们的研究结果表明，Bpa和Str是等位基因突变，并确定了第一个与X连锁显性、雄性致死表型相关的哺乳动物基因座。它们还扩展了与胆固醇代谢异常相关的表型谱。
• Interactions of the ergosterol biosynthetic pathway with other lipid pathways
  作者：C. Lang、M. Veen

  DOI：10.1042/bst20051178

  日期：2005.10.1

  Micro-organisms have recently received broad attention as sources of novel lipids. An increased understanding of the effects of fats and oils and their composition on the metabolism and on health has shifted the focus towards the use of lipids for disease treatment and prevention and for the promotion of good health. A large range of lipidic products produced by yeast is known today. Ergosterol and its metabolic precursors are major lipidic components of industrial and commercial interest. Having in mind the aim to increase the productivity of ergosterol and its precursor metabolites, both the knowledge of regulatory mechanisms of the biosynthetic pathway and its interactions with other lipid pathways like those of sphingolipids, phospholipids and fatty acids are crucial.
• Rahimtula A.D.; Gaylor J.L., J Biol Chem, 1972, 0021-9258, 9-15
  作者：Rahimtula A.D.、Gaylor J.L.

  DOI：——

  日期：——